There is a certain day every October when I open my closet and finally reach for the tall boots I shoved to the back last spring. It feels like greeting an old friend, honestly.
My sister makes fun of me because I own more boots than sensible shoes, and she is not wrong. But there is nothing that makes me feel more put together than a good pair of boots pulled on over jeans or under a dress.
So I started jotting down all the combinations I love, and before I knew it I had a full list. If you are staring at your boots wondering how to wear them this season, this list is for you.
My Favorite Ways to Style Tall Boots This Season
Chocolate Boots With Knit Dress
Chocolate brown boots are so underrated. They go with more colors than black does, honestly, and they read as warm and cozy in a way that black never quite manages.
Pair them with a soft ribbed knit dress in cream or oatmeal and you have an outfit that looks like you tried, even though you rolled out of bed ten minutes ago.
Black High Boots With Miniskirt
The classic that never really goes anywhere. A black high boots outfit built around a little miniskirt is the sort of look I reach for when I want to feel a bit daring but also warm, because the boots cover so much leg.
Add opaque tights underneath for the cooler months. And a chunky sweater tucked in at the front so the skirt still shows.
Givenchy Boots With Leather Blazer
Okay, so not everyone owns designer boots, and neither do I, if I am being honest. But if you have a sleek pointed pair (Givenchy-style or otherwise), lean into the polish.
A structured leather blazer over a simple top, slim trousers, and those boots. It’s the kind of outfit my friend Dana wears to work meetings and then straight out to dinner without changing a single thing. She swears by it.
White Boots With Denim Midi Skirt
White boots feel a little unexpected, which is exactly why I love them. They brighten up an outfit instantly and keep things from looking too heavy in the darker months.
A denim midi skirt is the perfect partner here. The length of the skirt and the height of the boots leave just a sliver of leg, which somehow looks so intentional and cool. Tuck in a fine-knit turtleneck and call it done.
Bootcut Jeans With Pointed Boots
Bootcut jeans exist for a reason, and that reason is pointed boots underneath them. The flare of the jean sits so nicely over the shaft of the boot, and you get this long, lean line from hip to toe.
I wore this all through last fall and got compliments every single time. In fact, I wore it so much my husband started calling it my uniform.
Hunter Boots With Quilted Jacket
Now for the practical entry. Hunter boots are not glamorous, but they are the boots I actually live in when the weather turns. Rainy school runs, muddy walks, the farmers’ market when the sky opens up.
A quilted jacket over jeans, those glossy rubber boots, and you look like you belong in the countryside even if you are just dashing to the car. So cozy, so easy, so ME on a Saturday morning.
Thigh-High Boots With Sweater Dress
Thigh-high boots have a reputation, but paired with an oversized sweater dress they are honestly one of the most comfortable things you can wear. The dress is roomy and warm, and the boots do all the shaping.
Go for a slouchy suede pair in a soft neutral. Nothing too shiny. You want it to feel effortless, not like a costume.
Tan Riding Boots With Leggings
Riding boots are the ones I keep coming back to year after year. They never date. They just quietly get better with age, scuffs and all.
Tan leather riding boots over black leggings, a long tunic top, and a scarf wrapped around your neck. This is my running-errands look, my picking-up-kids look, my everything look. And yes, I have owned the same pair for six years now.
Patent Boots With Pleated Miniskirt
Patent leather catches the light in the most lovely way, especially under grey autumn skies when you need a little shine. A patent boot with a pleated miniskirt is playful and a bit preppy.
Add a cropped sweater and you have a look that feels young and fun without trying too hard. My niece asked to borrow this exact outfit for a school event, which I took as a compliment.
Long Boots With Satin Dress
Here is where things get a little dressier. A long boots outfit paired with a slip-style satin dress is one of my favorite ways to make evening plans feel special without pulling out heels I can barely walk in.
The satin catches the light, the boots ground the look, and you can actually move around all night. I did this at a dinner party last winter and did not sit down once. My feet were fine. Truly a small miracle.
High Boots With Bermuda Shorts
This one surprised me. A high boots outfit with tailored bermuda shorts sounds odd on paper, but it works so well in that shoulder season when it is cold in the morning and warmer by lunch.
Wear opaque tights underneath if you get cold like I do. Then a blazer on top and you have something a little fashion-forward that still keeps you warm on the walk in.
Givenchy Boots With Monochrome Black
When in doubt, wear all black. It is the outfit equivalent of a deep breath. A sleek pair of designer-style boots with head-to-toe black looks expensive even when it is not.
Black trousers, black knit, a long black coat, and those boots peeking out at the bottom. That’s it. So simple, and somehow the most polished I ever feel.
White Boots With Flared Jeans
Back to white boots, because I really cannot get enough of them. This time with flared jeans for a bit of a retro moment.
The flare of the jean skims right over the boot, so you get little flashes of white as you walk. Add a fitted top and some gold earrings and you are channeling a very good decade of style, in the nicest way.
Bootcut Jeans With Suede Boots
Suede boots feel so soft and rich in the fall. Paired with bootcut jeans, they make an outfit that is casual but never sloppy.
Choose a warm cognac or camel suede. A cream sweater tucked loosely at the waist. And a cross-body bag because I am forever losing my hands to carrying things I do not need. Of course.
Hunter Boots With Trench Coat
My most-worn combination of the entire rainy season, if I am being completely honest with you. A trench coat and Hunter boots is the outfit that gets me out the door on the grey days when I would rather stay in.
Belt the trench at the waist so you do not look like you are drowning in fabric. Then let the boots do their job. Practical, a little bit chic, and dry. Always dry.
Thigh-High Boots With Blazer Dress
A blazer dress is one of those pieces that does most of the work for you, and thigh-high boots finish it off beautifully. Together they walk the line between smart and a little bit bold.
Keep the boots simple and matte so the blazer dress stays the star. This is what I would wear to a nice lunch that turns into an afternoon of wandering around shops, which is my favorite kind of day.
Brown Boots With Floral Midi Dress
Floral dresses are not just for spring, and I will defend this forever. A dark floral midi dress with brown boots feels autumnal and romantic all at once.
Layer a chunky cardigan over the top and add tights when it gets cold. The brown of the boots pulls out the warmer tones in the print, and the whole thing looks like a lovely walk through fallen leaves. My kind of outfit exactly.
Croc Boots With Tailored Shorts
Croc-embossed boots have this quiet luxury feeling to them. Paired with a set of tailored shorts, they lift an outfit into something a bit more considered.
Tights underneath, a fine knit tucked in, and a longer coat over the top. It is a look for the days when you want to feel a little bit dressed up but the calendar says it is still technically shorts weather.
Knee-High Boots With Cigarette Jeans
Cigarette jeans and knee-high boots were made for each other. The slim ankle of the jean slides right into the boot with no bunching, which is honestly half the battle with tall boots.
Tuck the hem in, throw on an oversized coat, and you have a look that works for basically anything. Coffee runs, dinner, a long overdue catch-up with an old friend. I have worn this to all three in the same week.
Slouchy Boots With Boho Dress
And last but not least, my most relaxed pairing of the lot. Slouchy suede boots with a flowy boho dress is the outfit I put on when I want to feel comfortable but still like myself.
The dress moves, the boots wrinkle in all the right places, and it comes together in about two minutes flat. I keep a version of this ready in my closet at all times, and I am never sorry that I do.
